65910-12-5Relevant academic research and scientific papers
Synthesis of 4-arylselanyl-1h-1,2,3-triazoles from selenium-containing carbinols
Alves, Diego,Balaguez, Renata A.,Begini, Francesca,Larroza, Allya,Lenard?o, Eder Jo?o,Lopes, Eric F.,Santi, Claudio
supporting information, (2021/05/28)
In this work, we present a simple way to achieve 4-arylselanyl-1H-1,2,3-triazoles from selenium-containing carbinols in a one-pot strategy. The selenium-containing carbinols were used as starting materials to produce a range of selanyl-triazoles in moderate to good yields, including a quinoline and Zidovudine derivatives. One-pot protocols are crucial to the current concerns about waste production and solvent consumption, avoiding the isolation and purification steps of the reactive terminal selanylalkynes. We could also isolate an interesting and unprecedented by-product with one alkynylselenium moiety connected to the triazole.
Redox-Neutral Synthesis of Selenoesters by Oxyarylation of Selenoalkynes under Mild Conditions
Baldassari, Lucas L.,Mantovani, Anderson C.,Senoner, Samuel,Maryasin, Boris,Maulide, Nuno,Lüdtke, Diogo S.
supporting information, p. 5881 - 5885 (2018/09/25)
An approach for the mild synthesis of selenoesters starting from selenoalkynes through an acid-catalyzed, redox-neutral oxyarylation reaction is reported. Br?nsted acid activation of a selenoalkyne leads to a selenium-stabilized vinyl cation, which is cap
Synthesis of Terminal Ethynyl Aryl Selenides and Sulfides Based on the Retro-Favorskii Reaction of Hydroxypropargyl Precursors
Lopes, Eric F.,Dalberto, Bianca T.,Perin, Gelson,Alves, Diego,Barcellos, Thiago,Lenard?o, Eder J.
supporting information, p. 13760 - 13765 (2017/09/08)
The retro-Favorskii reaction is an excellent way to achieve terminal alkynes. Methodologies that connect the synthesis of terminal alkynes and organochalcogen motifs are important for the construction of novel compounds. Fourteen new terminal alkynes containing either Csp?S or Csp?Se bonds were selectively prepared through the retro-Favorskii reaction from the respective carbinol precursors. It was discovered that terminal chalcogen alkynes were stable for weeks if stored as a solution in hexanes.
Ytterbium(III)-catalyzed three-component reactions: Synthesis of 4-organoselenium-quinolines
De Oliveira, Isadora M.,Vasconcelos, Stanley S. N.,Barbeiro, Cristiane S.,Correra, Thiago C.,Shamim, Anwar,Pimenta, Daniel C.,Caracelli, Ignez,Zukerman-Schpector, Julio,Stefani, Hélio A.,Manarin, Flávia
, p. 9884 - 9888 (2017/09/18)
4-Organoselenium-quinolines were synthesized via model multi-component Povarov (MCR) reactions between p-anisidine, ethyl glyoxylate and ethynyl(phenyl)selane, catalyzed by the Lewis acid Yb(OTf)3, with yields ranging from moderate to good. This method is advantageous in that there is no requirement for an oxidant and that the reaction has a wide scope. These 4-organoselenium-quinolines allowed access to 4-alkynyl-quinolines, which were synthesized via copper free Sonogashira cross-coupling reactions catalyzed by a new palladium catalyst that employs an oxazoline derivative as a ligand. A plausible mechanism was proposed based on HRMS studies.
A stereoselective route to (E)-1-alkylseleno-1-alkenes via hydroboration-iodination of terminal alkylselenoacetylenes with dicyclohexylborane
Yang, De-Yu,Huang, Xian
, p. 231 - 236 (2007/10/03)
(E)-1-Alkylseleno-1-alkenes 4 have been synthesized with higher stereoselectivity by hydroboration-iodination of terminal alkylselenoacetylenes with dicyclohexylborane.
Stereoselective synthesis of (E,E)-1-arylselenobutadienes by cross- coupling reactions in the presence of palladium catalyst
Zhu, Liu-Sheng,Huang, Zhi-Zhen,Huang, Xian
, p. 9819 - 9822 (2007/10/03)
Hydrozirconation of arylselenoethynes 1 gives selenium containing zirconium(IV) complexes 2, which are cross coupled with alkenyl halides in the presence of Pd (PPh3)4 to afford (E,E)-1-arylselenobutadienes 4 in high yields.
Regio- and stereoselective synthesis of (E)-1-alkylseleno-1,4-pentadienes by cross-coupling of allyl bromide with alkylselenovinylcoppers from alkylselenovinyldialkylboranes
Yang, De-Yu,Huang, Xian
, p. 4369 - 4373 (2007/10/03)
Alkylselenovinyldialkylborane derivatives, obtained by hydroboration of terminal alkylselenoacetylenes 1 with dialkylboranes 2, were treated at -15°C with sodium methoxide and cuprous bromide-methyl sulfide to generate alkylselenovinylcopper intermediates which underwent stereospecific cross-coupling with allyl bromide to yield (E)-1-alkylseleno-1,4-pentadienes 3. The compounds 3 were formed with retention of configuration predetermined from the stereochemistry of the initial alkylselenovinylboranes.
